Holiday rentals in Cockpit Island

Upscale Living 5BR 3BA | Near Ancaster Mill

Upscale 5BR Home in Scenic Ancaster Near Ancaster Mill Experience upscale living in this spacious 5-bedroom home featuring queen beds throughout, including a private master suite with ensuite. Enjoy 3 full bathrooms, 3 stylish living rooms with TVs, 2 fully equipped kitchens and 2 dining areas, plus 2 laundry spaces. A large backyard and multiple entrances add comfort and flexibility. Perfect for weddings, families, and group stays, just minutes from Ancaster Mill for unforgettable experiences.

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Private Suite Near Locke St

Enjoy a cozy experience at this centrally located place in a peaceful neighbourhood. Private entrance to a separate apartment. 2 bed 1 bathroom unit on the upper floors of a detached home. The main floor is occupied but there is no shared spaces. Located steps from Locke Street where you can find lots of trendy restaurants, cafe's and shopping. Park located within walking distance. Please review parking information. McMaster University and Children's Hospital within a 10-15 minute drive.

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Frenchman’s Pass - Cozy nook on the Hamilton brow

Welcome to your home away from home! This charming suite on the main floor of our home has a separate entrance and a private deck. Nestled on the Hamilton Mountain in one of Hamilton's most upscale neighborhoods, we are steps from the scenic brow offering the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking and essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping, restaurants, and public transit.

Fully-Furnished Boutique 1 Bedroom Suites

The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.

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Luxury Locke Street Loft

Stay in a beautifully renovated, two-level private loft in the heart of Hamilton. Located in a historic building on trendy Locke Street, you’re minutes from top restaurants, shops, and attractions. The space features 3 bedrooms and 2 full bathrooms, sleeping up to 8 guests. Enjoy an open-concept living area with a bar setup and 85” TV, plus free parking, in-suite laundry, and exclusive discounts at Beasley’s Bistro. Perfect for relaxing or entertaining after a day exploring the city.

Chic Oasis | Steps Away From TD Coliseum Hamilton

Step into a stunning modern-retro escape where bold red tones, playful pink accents, and vintage exposed red bricks create an unforgettable vibe. Perfectly located just steps from vibrant Hess Village, you're within walking distance to concerts, sports venues, art galleries, boutiques, and top-tier dining. Explore trendy Locke Street or hike the Escarpment nearby. With cozy bedrooms, chic outdoor spaces, and irresistible charm, this gem is a true city retreat.

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Summertime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

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Private Top-Floor Loft • Prime Hamilton Location

Bright, private top-floor suite in central Hamilton, just steps from Locke St and 2 blocks to the TD Coliseum. Walk to cafés, restaurants, and events at Bridgeworks, or explore nearby breweries, trails, and waterfalls. Only 3.5 km to McMaster University, 45 mins to Toronto, and 1 hr to Niagara Falls. Includes dedicated on-site parking. Hosted by an experienced Superhost offering a comfortable, reliable stay for both business and leisure travellers.

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

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Animal Lovers Dream! Barn Loft in Burlington

Experience life on a tiny farm just outside the city! Stay in our charming and comfortable barn loft and wake up to the sounds of chickens, ducks, geese, pigs, goats and horses and our adorable Highland cows. Spend time watching or interacting with all the very friendly animals that surround the barn. You will meet all the animals as they all come up readily to anyone who visits the farm. Guests are welcome to participate in the morning feeding.

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Gallery Suite

The Gallery Suite near Locke St. and McMaster is ideal for business or leisure stays. This bright, open-concept suite with a separate bedroom features unique artwork by Guelph artist Ryan Price. Located above a quiet RMT clinic, you'll enjoy a peaceful and private stay. Walking distance to trendy shops and cafes. Free parking is included for your convenience. Book now to experience a blend of comfort, art, and convenience!

Luxurious 5BR Beach House with Firepit

Spatious and luxirious house by the beach has 5 bedrooms with a large comfy sectional, enough to sleep 10 guests total. Our kitchen is fully stocked with everything you need to make grand dinners. We have a beautiful long custom designed dining table for memorable family gatherings. Enjoy serene views of the lake on our large furnished deck, where there is a large BBQ, dining area, sofa, and fire table.